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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H27NO2
Molecular Weight 337.4553
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOBELINE, (+)-

SMILES

CN1[C@@H](C[C@@H](O)C2=CC=CC=C2)CCC[C@H]1CC(=O)C3=CC=CC=C3

InChI

InChIKey=MXYUKLILVYORSK-QHAWAJNXSA-N
InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m1/s1

HIDE SMILES / InChI
Lobeline,(+)- is unnatural enantiomer of Lobeline. Lobeline is the main active alkaloid constituent of Lobelia inflata, a plant sometimes called “Indian tobacco” because it was initially used by Indians of North America as a tobacco substitute. The crude extract is toxic but has been widely recommended for treatment of respiratory illnesses such as asthma, bronchitis, pneumonia, and whooping cough.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.3 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Enantioselective synthesis of lobeline via nonenzymatic desymmetrization.
2007-08-16
Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations.
2005-10-19

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
LOBELINE, (+)-
Common Name English
(+)-LOBELINE
Preferred Name English
ETHANONE, 2-((2S,6R)-6-((2R)-2-HYDROXY-2-PHENYLETHYL)-1-METHYL-2-PIPERIDINYL)-1-PHENYL-
Systematic Name English
Code System Code Type Description
PUBCHEM
5288703
Created by admin on Mon Mar 31 22:21:09 GMT 2025 , Edited by admin on Mon Mar 31 22:21:09 GMT 2025
PRIMARY
FDA UNII
74SSN124VK
Created by admin on Mon Mar 31 22:21:09 GMT 2025 , Edited by admin on Mon Mar 31 22:21:09 GMT 2025
PRIMARY
CAS
246018-80-4
Created by admin on Mon Mar 31 22:21:09 GMT 2025 , Edited by admin on Mon Mar 31 22:21:09 GMT 2025
PRIMARY